CN101558128B - Peroxide-curable silicone-based pressure-sensitive adhesive composition and adhesive tape - Google Patents
Peroxide-curable silicone-based pressure-sensitive adhesive composition and adhesive tape Download PDFInfo
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- CN101558128B CN101558128B CN2007800457284A CN200780045728A CN101558128B CN 101558128 B CN101558128 B CN 101558128B CN 2007800457284 A CN2007800457284 A CN 2007800457284A CN 200780045728 A CN200780045728 A CN 200780045728A CN 101558128 B CN101558128 B CN 101558128B
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- sensitive adhesive
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2483/00—Presence of polysiloxane
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2852—Adhesive compositions
Abstract
A peroxide-curable silicone-based pressure-sensitive adhesive composition comprising (A) a diorganopolysiloxane having silicon-bonded alkenyl groups at both molecular terminals used in amount of 100 parts by weight; (B) an organopolysiloxane resin having one or more silanol(OH) groups in one molecule and consisting of R32(OH)SiO1/2 units (where R3 independently stands for non-substituted or substituted monovalent hydrocarbon groups having 1 to 10 carbon atoms), R3 3 SiO1/2 units (wherein R3 is the same as defined above), and SiO4/2 units, used in amount of 10 to 200 parts by weight; and (C) one or more types of organic peroxide compounds used in a catalytic quantity.
Description
Technical field
The present invention relates to have the silicone-based pressure-sensitive adhesive composition of the peroxide-curable of ultralow siloxanes transfer performance, it in addition under being exposed to high temperature after, can also keep good binding property, after peeling off, prevent from producing adhesive residue and silicone components at adherend almost ideally.The invention still further relates to the self adhesive tape that uses aforementioned silicone-based pressure-sensitive adhesive composition.
Background technology
Compare with acrylic or rubber-based pressure-sensitive adhesive composition, silicone-based pressure-sensitive adhesive composition is better than that the former part is its electrical isolation, heat-resisting, weather resistance and to the binding property of various substrates.Depend on curing mechanism, aforementioned silicone-based pressure-sensitive adhesive composition can be divided into the composition that solidifies by addition reaction, the composition that solidifies by condensation reaction, the perhaps composition by peroxide cure.Especially, the silicone-based pressure-sensitive adhesive composition of peroxide-curable is favourable, because in solidification process, and can be by regulating the physicals of regulating the pressure sensitive adhesive layer that is formed by said composition as the consumption of the organo-peroxide of catalyzer.The silicone-based pressure-sensitive adhesive composition of this peroxide-curable is disclosed in Japanese patent publication H07-70540 (references 1) or Japanese patent publication H07-53941 (references 2), and exemplify in these patents can be by the organopolysiloxane with silanol group, the organopolysiloxane resins that contains silanol group, the silicone-based pressure-sensitive adhesive composition of the peroxide-curable that organo-peroxide and organic solvent form.In addition, they also disclose and have had silanol group and the optional organopolysiloxane with alkenyl.
The silicone-based pressure-sensitive adhesive composition of known these peroxide-curables has some shortcomings, for example make adherend oxidation and variable color, particularly when they for the preparation of in electricity and field of electronic materials, use require high heat resistance can self adhesive tape the time, especially prepare heat resistant adhesive tape, electrical insulating tape, heat seal adhesive tape, plating masking belt, when being used for the masking belt etc. of heat treatment operation.For the great majority of the aforementioned adhesion band of intending using with the metal adherend, the stickup interface between adhesive tape and the metal is exposed under the organo-peroxide and degradation production thereof as catalyzer.Therefore, the adherend surface is easy to oxidation, variable color or similar impact.Owing to this reason, normally used self adhesive tape mainly is the silicone-based pressure-sensitive adhesive composition (for example, referring to Japanese patent publication H04-335083 (references 3) and Japanese patent publication H10-110156 (references 4)) of addition curing in electricity and field of electronic materials.
Although can use take the substrate of stainless steel plate or metal-plated as the anti-superoxide of example and the substrate of degradation production limits this oxidation and variable color, but another problem that the aforementioned adhesion band has is, when peeling off them, stay easily adhesive residue and shift silicone components to the adherend surface of these antioxidants.
On the other hand, proposed in curable silicone-based pressure-sensitive adhesive composition in conjunction with the curing mechanism and the curing mechanism of addition reaction type or the curing mechanism (referring to Japanese patent publication H04-335083 (references 5), H10-324860 (references 6), H05-214316 (references 7) and 2004-506778 (references 8)) of condensation reaction type that utilize the superoxide type.In these systems, disclose curing composition and comprised the organopolysiloxane with alkenyl, organic radical hydrogen polysiloxanes or contain the organopolysiloxane of silanol is by R
3SiO
1/2Unit and SiO
4/2The organopolysiloxane resins that the unit forms, hydrosilylation catalysts or silanol-reaction catalyst, organo-peroxide and organic solvent.
Yet, when these the known self adhesive tapes with silicone-based pressure-sensitive adhesive layer use because of its resistance toheat and after the release adhesive band, on substrate surface, still can observe visually residual micro siloxane, and be absolutely necessary with the operation bidirectional of organic solvent clean surface.Therefore, need exploitation to stay the pressure sensitive adhesive of the residual silicone components of in fact invisible amount at substrate surface, in order to can save the step with organic solvent clean substrate surface, especially when in the heat treatment operation process of solder reflows treatment circuit plate, when aforementioned adhesive tape is used as masking belt.
State before use in the situation of disclosed silicone-based pressure-sensitive adhesive composition in the patent documentation, after in equaling or exceeding 250 ℃ the hot environment of temperature, keeping, can not be limited in the residual tackiness agent of formation on the adherend surface, and can not save subsequently with organic solvent cleaning adherend surface to so that can prevent the adherend surface discolouration and eliminate the degree that residual siloxanes exists on the adherend surface fully.
Disclosure of the Invention
The silicone-based pressure-sensitive adhesive composition that the purpose of this invention is to provide peroxide-curable, it obtains having the pressure sensitive adhesive layer of ultralow siloxanes transfer performance, human eye can not detect adhesive residue as a result, even and being equal to or greater than it is exposed under the thermal treatment under 250 ℃ the temperature, do not shift silicone components yet.Another purpose provides the self adhesive tape based on aforementioned adhesion agent composition, the masking belt that especially uses in thermal treatment process.
By the silicone-based pressure-sensitive adhesive composition of the peroxide-curable that comprises the following component that provides (A)-(C), and solve these problems of prior art by the self adhesive tape with the pressure sensitive adhesive layer that obtains by the silicone-based pressure-sensitive adhesive composition that solidifies aforementioned peroxide-curable: (A) consumption be 100 weight parts with the diorganopolysiloxaneand of on two molecular end, all having of representing of general formula (1) with the alkenyl of silicon bonding:
(R wherein
1The monovalent saturated hydrocarbon group that expression does not replace or replaces, R
2Expression has the alkenyl of 2-10 carbon atom, and k is equal to or greater than 2000 integer, and s is 0 or positive integer, and they satisfy following condition: 0.0≤s/ (k+s)≤0.02); (B) consumption be the 10-200 weight part in a molecule, have one or more silanol groups (OH) and by R
3 2(OH) SiO
1/2Unit (R wherein
3Expression has the univalence hydrocarbyl of not replacing of 1-10 carbon atom or replacement independently), R
3 3SiO
1/2Unit (R wherein
3Identically with above definition) and SiO
4/2The organopolysiloxane resins that the unit forms; (C) one or more superoxide based compounds of catalytic amount.
More specifically, the invention provides: the silicone-based pressure-sensitive adhesive composition of [1] a kind of peroxide-curable, it comprises component (A)-(C), wherein: (A) consumption be 100 weight parts on two molecular end, all have a diorganopolysiloxaneand with the alkenyl of silicon bonding with general formula (1) expression:
(R wherein
1The monovalent saturated hydrocarbon group that expression does not replace or replaces, R
2Expression has the alkenyl of 2-10 carbon atom, and k is equal to or greater than 2000 integer, and s is 0 or positive integer, and they satisfy following condition: 0.0≤s/ (k+s)≤0.02); (B) consumption be the 10-200 weight part in a molecule, have one or more silanol groups (OH) and by R
3 2(OH) SiO
1/2Unit (R wherein
3Expression has the univalence hydrocarbyl of not replacing of 1-10 carbon atom or replacement independently), R
3 3SiO
1/2Unit (R wherein
3Identically with above definition) and SiO
4/2The organopolysiloxane resins that the unit forms; (C) one or more organic peroxide compounds of catalytic amount.[2] silicone-based pressure-sensitive adhesive composition of the peroxide-curable in the clauses and subclauses [1], wherein aforementioned component (B) is R
3 2(OH) SiO
1/2Unit and R
3 3SiO
1/2Unit sum and SiO
4/2The organopolysiloxane resin of the ratio of unit in the 0.5-1.2 scope.[3] silicone-based pressure-sensitive adhesive composition of the peroxide-curable in the clauses and subclauses [1], wherein aforementioned component (B) is that 90-99.5mol% is that methyl and 0.5-10mol% are the organopolysiloxane resins of silanol group in the middle of all functional groups that wherein comprise in this component.[4] silicone-based pressure-sensitive adhesive composition of the peroxide-curable of clauses and subclauses [1]-[3] in any one further comprises organic solvent (D).[5] a kind of self adhesive tape, it comprises carrier film and the pressure sensitive adhesive layer that obtains by the silicone-based pressure-sensitive adhesive composition that solidifies the peroxide-curable of clauses and subclauses [1]-[4] in any one.[6] self adhesive tape in the clauses and subclauses [5], it is the masking belt that uses in thermal treatment.[7] self adhesive tape in the clauses and subclauses [5] wherein uses in the processing of aforementioned masking belt plan under 200-300 ℃ temperature.
The invention effect
The present invention can provide the silicone-based pressure-sensitive adhesive composition of peroxide-curable, it obtains having the pressure sensitive adhesive layer of ultralow siloxanes transfer performance, human eye can not detect adhesive residue as a result, even and when repeatedly peeling off after under being equal to or greater than 250 ℃ temperature, being exposed to thermal treatment, do not shift silicone components yet.Can provide self adhesive tape based on this composition, the masking belt that especially in thermal treatment process, uses with the present invention.
Detailed Description Of The Invention
At first, at length explain the silicone-based pressure-sensitive adhesive composition of peroxide-curable of the present invention.This composition comprises (A) and all have diorganopolysiloxaneand with the height polymerization of content in specialized range of the alkenyl of silicon bonding and these groups on two molecular end, (B) have the organopolysiloxane resins of silanol group, and (C) organic peroxide compounds.By using these components of specified amount, after peeling off, be implemented in and prevent almost completely on the adherend that silicone components from shifting and adhesive residue.
Component (A) is one of concrete component of the present invention.This component be all have on two molecular end with the alkenyl of silicon bonding and with below the diorganopolysiloxaneand of general formula (1) expression that provides:
(R wherein
1The monovalent saturated hydrocarbon group that expression does not replace or replaces, R
2Expression has the alkenyl of 2-10 carbon atom, and k is equal to or greater than 2000 integer, and s is 0 or positive integer, and they satisfy following condition: 0.0≤s/ (k+s)≤0.02).The component (B) of the diorganopolysiloxaneand by being combined with component of the present invention (A) (it all has with the alkenyl of silicon bonding on two molecular end and has the predetermined polymerization degree and the alkenyl of predetermined amount) and the following stated, after repeatedly peeling off, can prevent from almost completely that silicone components from transferring on the adherend surface and at adherend to form adhesive residue.
In following formula, R
1The monovalent saturated hydrocarbon group that expression does not replace or replaces.The specific examples of these groups is following: methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, the tertiary butyl, amyl group, neo-pentyl, hexyl, heptyl, octyl group, nonyl, decyl, dodecyl or similar alkyl; Phenyl, tolyl, xylyl, naphthyl, xenyl or similar aryl; Cyclopentyl, cyclohexyl, suberyl or loop-like alkyl; Benzyl, styroyl, hydrocinnamyl, methyl-benzyl or similar aralkyl; Or wherein the one or more hydrogen atoms in the monovalent saturated hydrocarbon group by the halogen atom aforementioned group that replaces of fluorine atom, chlorine atom, bromine atoms or other halogen atoms and cyano group for example.The example of this [replacement] group is following: chloro methyl, 2-bromotrifluoromethane, 3-chloropropyl, 3,3,3-trifluoro propyl, chloro-phenyl-, fluorophenyl, cyanoethyl, 3,3,4,4,5,5,6,6,6-nine fluorine hexyls etc.Consider most preferable and phenyl from the production angle.R
2Expression has the alkenyl of 2-10 carbon atom.But this group exemplified by vinyl, allyl group, propenyl, pseudoallyl, butenyl, pentenyl, hexenyl, cyclohexenyl or similar group.The alkenyl that most preferably has 2-6 carbon atom, especially vinyl and hexenyl.
In following formula, k is equal to or greater than 2000 integer, and the expression polymerization degree.The scope of preferred k is 2000-100,000.If the polymerization degree k of component (A) is lower than 2000, then can not obtain the pressure sensitive adhesive layer with enough low adhesive transfer performances.In addition, the polymerization degree s with siloxane unit component of alkenyl equals 0 or positive integer, and polymerization degree k and s the two should satisfy following condition: 0≤s/ (k+s)≤0.02.If s/ (k+s) surpasses recommended upper limit, even the component (C) of then regulating the following stated that consists of curing catalysts also can not form stable pressure sensitive adhesive layer to an amount of, perhaps can not provide fully bonding to substrate of pressure sensitive adhesive layer.If component (A) does not contain the alkenyl with 2-10 carbon atom on two molecular end, then in fact can not provide the pressure sensitive adhesive layer with enough low adhesive transfer performances.Most preferred composition (A) has only two alkenyls with 2-10 carbon atom two molecular end.
The viscosity of preferred ingredient (A) under 25 ℃ is equal to or greater than 50,000mPa.s, and more preferably greater than 100,000mPa.s, and comprises the liquid organopolysiloxane or have the organopolysiloxane (it is called as so-called thick silicon rubber) of degree of moulding.
Component (B) is by R
3 2(OH) SiO
1/2Unit, R
3 3SiO
1/2Unit and SiO
4/2The organopolysiloxane resins that the unit forms.This component contains one or more silanol groups (OH) at a molecule.Consider all functional groups that preferably in component (B), comprise, i.e. silanol group (OH) and use R from the angle of the low adhesive transfer performance by solidifying the pressure sensitive adhesive layer that composition of the present invention obtains
3In the middle of functional group's sum of expression, the 0.5-10mol% of all functional groups of silanol fiduciary point, preferred 1-5mol%.R
3Expression has the univalence hydrocarbyl that does not replace or replace of 1-10 carbon atom independently.The specific examples of this group is following: methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, the tertiary butyl, amyl group, neo-pentyl, hexyl, heptyl, octyl group, nonyl, decyl, dodecyl or similar alkyl; Phenyl, tolyl, xylyl, naphthyl, xenyl or similar aryl; Cyclopentyl, cyclohexyl, suberyl or loop-like alkyl; Benzyl, styroyl, hydrocinnamyl, methyl-benzyl or similar aralkyl; Vinyl, allyl group, propenyl, pseudoallyl, butenyl, pentenyl, hexenyl, cyclohexenyl or chain-like thiazolinyl; Or wherein the one or more hydrogen atoms in the univalence hydrocarbyl by the halogen atom aforementioned group that replaces of fluorine atom, chlorine atom, bromine atoms or other halogen atoms and cyano group for example.The example of this [replacement] group is following: chloro methyl, 2-bromotrifluoromethane, 3-chloropropyl, 3,3,3-trifluoro propyl, chloro-phenyl-, fluorophenyl, cyanoethyl, 3,3,4,4,5,5,6,6,6-nine fluorine hexyls etc.Consider most preferable from the production angle.The content range of preferable methyl is all aforementioned functional groups and the R that represents with silanol group (OH) in the component (B)
3The 90-99.5mol% of functional group's sum of expression, preferred 90-99mol%.
In component (B), R
3 2(OH) SiO
1/2And R
3 3SiO
1/2Unit sum and SiO
4/2The molar ratio range of unit should be 0.5-1.2, and preferable range is 0.6-0.9.If R
3 2(OH) SiO
1/2And R
3 3SiO
1/2Unit sum and SiO
4/2The mol ratio of unit is lower than upper recommended limit, and then the viscosity of pressure sensitive adhesive descends.If aforementioned molar ratio surpasses recommended upper limit, then tend to reduce force of cohesion (maintenance intensity).
Need in the pressure sensitive silicone based adhesive compositions of peroxide-curable, in per 100 parts by weight of component (A), use consumption to be the 10-200 weight part, the component (B) of preferred 25-100 weight part.If the consumption of component (B), then can not provide the binding property of the pressure sensitive adhesive layer abundance that obtains by the curing silicone based pressure-sensitive adhesive composition less than above-mentioned lower limit; If surpass the above-mentioned upper limit with the content of this component, then after thermal treatment, a part of component (B) is retained on the adherend surface, does not therefore realize purpose of the present invention.
Component (C) is at least a organic peroxide compounds, and it is as the catalyzer of the pressure sensitive silicone based adhesive compositions that solidifies peroxide-curable.More specifically, this catalyzer can comprise the crosslinkable silicon curing catalysts that is comprised of the organopolysiloxane that has at least two alkenyls in a molecule, comprises that perhaps the component (B) of the organopolysiloxane that contains silanol group is used curing catalysts.(C) is not particularly limited to component, as long as it uses with organic peroxide compounds on curing system.The example of this curing catalysts is following: benzoyl peroxide, peroxidation 4-monochloro benzoyl, dicumyl peroxide, t-butylperoxyl benzoate, tert-butyl peroxide cumyl, tert-butyl peroxide, 2,5-dimethyl-2, the 5-di-t-butyl is crossed hexane, peroxidation 2,4-dichloro-benzoyl, the diperoxy tertiary butyl-diisopropyl benzene, 1, two (t-butylperoxy)-3 of 1-, 3,5-trimethyl-cyclohexane, 2,5-diperoxy tertiary butyl hexane-3,2,5-dimethyl-2, two (t-butylperoxy) hexanes of 5-, or the peroxidation cumyl tertiary butyl.Can use these catalyzer separately or in conjunction with two or more.Benzoyl peroxide most preferably.
Consumption to the component (C) that can use in the silicone-based pressure-sensitive adhesive composition of peroxide-curable is not particularly limited, if use scope can accelerate under as 50-200 ℃ heating condition component (A) and (B) between the component (C) of catalytic amount of curing reaction.Yet, consider that from actual angle in per 100 parts by weight of component (A) and (B) sum, preferably consumption is the 0.2-3.0 weight part, and more preferably 0.5-2.0 weight part.If the consumption of component (C) then solidifies insufficient less than upper recommended limit.On the other hand, if the consumption of component (C) surpasses recommended upper limit, then after thermal treatment, organic peroxide compounds or its degradation production will remain on the surface of adherend.This organic peroxide compounds can cause oxidation, variable color or form adhesive residue on the adherend surface, perhaps can accelerate silicone components and transfer on the adherend surface.Therefore, do not realize purpose of the present invention.
In the scope of not disturbing the object of the invention, the silicone-based pressure-sensitive adhesive composition of peroxide-curable also can further comprise some optional components except comprising component (A)-(C).A kind of such component exemplifies organic solvent (D) or other various types of conventional additives that use.
But the silicone-based pressure-sensitive adhesive composition that mixed peroxides is curable and organic solvent (D) or in organic solvent (D) with its dispersion.This organic solvent can be with following for representative: toluene, dimethylbenzene or similar aromatic hydrocarbon solvent; Hexane, octane, different paraffins or similar aliphatic hydrocarbon solvent; Acetone, methylethylketone, methyl iso-butyl ketone (MIBK) or similar ketone-based solvent; Ethyl acetate, isobutyl acetate or similar ester group acetic ester; Di Iso Propyl Ether, Isosorbide-5-Nitrae-dioxs or similar ether solvent; Hexamethyl cyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentaandoxane or polymerization degree scope are the similar cyclic polysiloxanes of 3-6, and trieline, tetrachloroethylene, trifluoromethylbenzene, 1, two (trifluoromethyl) benzene of 3-, methyl penta fluoro benzene or similar halohydrocarbon.Preferred toluene, dimethylbenzene or similar aromatic hydrocarbon solvent; Hexane, octane, different paraffins or similar aliphatic hydrocarbon solvent.Most preferably toluene or dimethylbenzene.Can two or more form of mixtures use these solvents.The operable consumption of aforementioned organic solvent to component (D) is not particularly limited, but usually, but recommendation is in the consumption of the total amount 5-1000 weight part of per 100 parts by weight of component (A)-(C).
By mixing aforementioned component (A)-(C) and one or more aforementioned arbitrarily components optionally, prepare the silicone-based pressure-sensitive adhesive composition of peroxide-curable of the present invention.Can by using known various agitators or mixing tank, mix equably these components.Be to mix under 0-20 ℃ the temperature in scope.The preparation of composition can form by only mix these components in the situation of the interpolation order that is not particularly limited each component.Yet, if composition does not plan directly to use immediately, can only prepare mixture by component (A), (B) and organic solvent (D) after preparation, and can be independent of component (C) storage for only before using, mixing with the latter.
Can by be applied in the substrate and at room temperature or under 150-220 ℃ temperature by being heating and curing, thereby preparation is by the pressure sensitive adhesive layer of the peroxide-curable that solidifies silicone-based pressure-sensitive adhesive composition of the present invention and obtain.Can pass through photogravure coating machine, letterpress print coater, compensating tank roll-coater, roller coating machine, reverse coater, air knife doctor knife coater, curtain coater or comma (comma) coating machine, apply composition.
It below is the more detailed description of self adhesive tape of the present invention.Self adhesive tape of the present invention is characterised in that to have the pressure sensitive adhesive layer that forms by the silicone-based pressure-sensitive adhesive composition that solidifies above-mentioned peroxide-curable of the present invention in the carrier film substrate.
The substrate of preferred vector film has high resistance toheat and can tolerate in the thermal treatment that is equal to or greater than under 200 ℃ the temperature.The example that is suitable for the material of this film is following: polyimide (PI), polyether-ether-ketone (PEEK), Polyethylene Naphthalate (PEN), the poly-arylide of liquid crystal, polyamidoimide (PAI), polyethers thioether (PES) or similar resin molding, and aluminium foil, Copper Foil or similar tinsel.Thickness to film is not particularly limited, but thickness range is the 5-300 micron usually.In addition, in order to improve pressure sensitive adhesive layer to the tight bond of film substrate, the substrate of available priming paint coated film is perhaps carried out Corona discharge Treatment, etching, itro processing or plasma treatment to the film substrate.
Can be by apply the silicone-based pressure-sensitive adhesive composition of peroxide-curable of the present invention in the aforementioned films substrate, then under 70-120 ℃ temperature, coating is carried out preliminarily dried, and after drying process be to heat under 150-220 ℃ the temperature at room temperature or in scope, solidify this layer, so form pressure sensitive adhesive layer in the film substrate, thereby preparation self adhesive tape.Applying method can be with above-mentioned identical.Preferably by the silicone-based pressure-sensitive adhesive composition that is heating and curing, and be heating combination under 160-200 ℃ the temperature in scope preferably.The consumption of composition to be applied depends on specific application, but typically after solidifying, the thickness range of pressure sensitive adhesive layer should be the 2-200 micron, and uses for masking belt, and thickness range should be the 5-50 micron.
Self adhesive tape of the present invention has good resistance toheat, when stripping tape, prevents from forming the binder substance of the silicone-based pressure-sensitive adhesive composition that contains peroxide-curable, and has almost completely eliminated silicone components and transferred on the adherend.Therefore, self adhesive tape of the present invention is suitable for as heat resistant adhesive tape, electrical insulating tape, heat seal adhesive tape, shikishima plating process with masking belt, thermal treatment with masking belt or other similar application.Especially, self adhesive tape of the present invention is particularly suitable for as heat treated masking belt or is 200-300 ℃ in scope, under preferred 250-300 ℃ the temperature, and the temporary fixed adhesive tape that in solder reflows technique, uses.
Embodiment
With reference to practical example and Comparative Examples, further describe in more detail the present invention, but be to be understood that these embodiment should not be interpreted as limiting the possible range of application of the present invention.In an embodiment, evaluation [adhesive residue that stays in substrate after under being exposed to high temperature and the transfer of silicone components] has been described below, and the method for its [bounding force].In practical example and Comparative Examples, Me represents methyl, and Vi represents vinyl.All percentage ratios (%) are wt%.[bounding force] is applied to silicone-based pressure-sensitive adhesive composition in the substrate of being made by polyimide resin (PI), and its consumption is so that after solidifying, the thickness of the pressure sensitive adhesive layer of formation is about 15 microns.By under 180 ℃, heating resulting products 2 minutes, form adhesive sheet.Afterwards, by laminator, the gained adhesive sheet is placed on the stripping film, and in baking oven, aging these laminate structures are 1 day under 50 ℃.After cool to room temperature, to become width be the rectangular of 20mm by cutting this aging sheet material, and suprabasil self adhesive tape is being peeled off in preparation.Then peel off self adhesive tape at the bottom of the stripping group, and by from rubber rollers, applying 2kg power, paste on the adherend of mirror face stainless steel sheet material (SUS304).Afterwards, keep adhesive tape 30 minutes at adherend, then adopt tester for elongation, measuring bounding force under the constant peeling rate of 300mm/min and under the peel angle of 180 degree.[after under being exposed to high temperature adhesive residue that substrate stays and the transfer of silicone components] is applied to silicone-based pressure-sensitive adhesive composition in the substrate of being made by polyimide resin (PI), its consumption is so that after solidifying, the thickness of the pressure sensitive adhesive layer of formation is about 15 microns.By under 180 ℃, heating resulting products 2 minutes, form adhesive sheet.Afterwards, by laminator, the gained adhesive sheet is placed on the stripping film, and in baking oven, aging these laminate structures are 1 day under 50 ℃.After cool to room temperature, to become width be the rectangular of 20mm by cutting this aging sheet material, and suprabasil self adhesive tape is being peeled off in preparation.Then peel off self adhesive tape at the bottom of the stripping group, and by from rubber rollers, applying 2kg power, paste on the adherend of glass epoxy board of mirror face stainless steel sheet material (SUS304) or gold-plated coating copper.Afterwards, in baking oven, the laminate structures of 250 ℃ of lower aging adherends 10 minutes, then at room temperature kept 30 minutes at adherend.By adopting tester for elongation, under the peel angles of the constant peeling rate of 300mm/min and 180 degree, peel off the self adhesive tape that is stuck, thereby estimate the adhesive residue that stays in substrate and the transfer of silicone components.According to following standard, estimate by human eye: zero: do not have residual any adhesive residue, do not have the silicone adhesive layer △ of trace with the surface at adherend: do not have residual any adhesive residue, and on the surface of adherend, only exist the silicone adhesive layer of trace *: adhesive residue is observed on the surface at adherend.
Practical example 1 is by mixing following component, the silicone-based pressure-sensitive adhesive composition P1:(A for preparing the peroxide-curable with 33wt% organopolysiloxane component) diorganopolysiloxaneand (molecular-weight average=296,800 that only have vinyl two molecular end shown in the average structure formula that provides below the 28.0 weight parts usefulness; Vinyl %=0.06): ViMe
2SiO (Me
2SiO)
4000SiMe
2The toluene solution of Vi (B) 16.4 weight parts, its have shown in the following average structure formula of 73.1 weight parts by Me
3SiO
1/2Unit, HOMe
2SiO
1/2Unit and SiO
4/2Organopolysiloxane resins (molecular-weight average=4605 that the unit forms; Solid matter with OH base content=1.11wt%): { Me
3SiO
1/2}
27{ HOMe
2SiO
1/2}
3{ SiO
4/2}
36(C) 2.0 weight part benzoyl peroxides (Nippon Oil and Fats Co., the product of Ltd.; Nyper BMT-K40); 2.0 weight part dimethylbenzene; With 73.5 parts by weight of toluene.With gained silicone-based pressure-sensitive adhesive P1 for the preparation of self adhesive tape.By with above-described same procedure, estimate bounding force and the siloxanes transfer performance of this self adhesive tape.
Practical example 2 prepares the silicone-based pressure-sensitive adhesive P2 of peroxide-curable with the method identical with practical example 1, difference be with 28.0 weight parts with below shown in the average structure formula that provides on its molecular end and have diorganopolysiloxaneand (molecular-weight average=298,500 of vinyl at its molecular side chain; Vinyl %=0.20) alternative compositions (A): ViMe
2SiO (Me
2SiO)
4000(ViMeSiO)
20SiMe
2Vi with gained silicone-based pressure-sensitive adhesive P2 for the preparation of self adhesive tape.By with above-described same procedure, estimate bounding force and the siloxanes transfer performance of this self adhesive tape.
Practical example 3 obtains the organopolysiloxane component concentration as the silicone-based pressure-sensitive adhesive composition P3 of the peroxide-curable of 33wt% take the method identical with practical example 1, difference be with 28.0 weight parts with below shown in the average structure formula that provides on its molecular end and have diorganopolysiloxaneand (molecular-weight average=300,223 of vinyl at its molecular side chain; Vinyl %=0.38) alternative compositions (A): ViMe
2SiO (Me
2SiO)
4000(ViMeSiO)
40SiMe
2Vi with gained silicone-based pressure-sensitive adhesive P3 for the preparation of self adhesive tape.By with above-described same procedure, estimate bounding force and the siloxanes transfer performance of this self adhesive tape.
Comparative Examples 1 obtains the organopolysiloxane component concentration as the silicone-based pressure-sensitive adhesive C1 of the peroxide-curable of 33wt% take the method identical with practical example 1, difference is diorganopolysiloxaneand (molecular-weight average=296,784 that all have silanol group on two molecular end shown in the average structure formula that provides below using with 28.0 weight parts; Silanol group %=0.01) alternative compositions (A): (HO) Me
2SiO (Me
2SiO)
4000SiMe
2(OH) with gained silicone-based pressure-sensitive adhesive C1 for the preparation of self adhesive tape.By with above-described same procedure, estimate bounding force and the siloxanes transfer performance of this self adhesive tape.
Comparative Examples 2 obtains the organopolysiloxane component concentration as the silicone-based pressure-sensitive adhesive C2 of the peroxide-curable of 33wt% take the method identical with practical example 1, difference be with 16.4 weight parts have shown in the average structure formula that provides below the 73.1 weight parts usefulness by Me
3SiO
1/2Unit and SiO
4/2The toluene solution alternative compositions (B) of the solid matter of the organopolysiloxane resins (molecular-weight average=4599) that the unit forms: { Me
3SiO
1/2}
30{ SiO
4/2}
36With gained silicone-based pressure-sensitive adhesive C2 for the preparation of self adhesive tape.By with above-described same procedure, estimate bounding force and the siloxanes transfer performance of this self adhesive tape.
Comparative Examples 3 is by mixing following component, the silicone-based pressure-sensitive adhesive composition C3:(a for preparing the peroxide-curable with 33wt% organopolysiloxane component) two molecular end shown in the average structure formula that provides below the 1.2 weight parts usefulness are all used the methyl hydrogen/dimethyl polysiloxane (H atom %=1.0, viscosity is 55mPa.s) of trimethylsiloxy end-blocking: Me
3SiO (Me
2SiO)
24(MeHSiO)
50SiMe
3(b) 31.8 weight parts with below shown in the average structure formula that provides on its molecular end and have diorganopolysiloxaneand (molecular-weight average=300,000 of vinyl at molecular side chain; Vinyl %=0.06): ViMe
2SiO (Me
2SiO)
4000(ViMeSiO)
5SiMe
2The toluene solution of Vi (c) 20.0 weight parts, its have 68.1 weight parts with below the average structure formula that provides represent by Me
3SiO
1/2Unit and SiO
4/2Unit (Me
3SiO
1/2Unit and SiO
4/2Mol ratio equal 0.8/1) solid matter of the organopolysiloxane resins that forms: { Me
3SiO
1/2}
30{ SiO
4/2}
36(d) 1,3-divinyl-1,1,3, the Platinic chloride complex compound of 3-tetramethyl disiloxane, its consumption is so that in weight unit, in the gross weight of component (a)-(c), the content of the metal platinum in the complex compound is 100ppm; 1.65 weight part dimethylbenzene; With 91.7 parts by weight of toluene.With gained silicone-based pressure-sensitive adhesive C3 for the preparation of self adhesive tape.By with above-described same procedure, estimate bounding force and the siloxanes transfer performance of this self adhesive tape.
The evaluation result that obtains in practical example 1-3 and Comparative Examples 1-3 has been shown in the table 1.Particularly in practical example 1-2, even the silicone-based pressure-sensitive adhesive composition that contains component (A)-(C) as the present invention is when being used for heat-resisting application, composition also provides sufficient bounding force, do not change its outward appearance, can in the situation that does not stay adhesive residue, peel off, and prevent that almost completely it from shifting silicone components to the adherend surface.On the other hand, be different from use in Comparative Examples 1 situation of other diorganopolysiloxaneands of component of the present invention (A), use therein in the situation of Comparative Examples 2 of other organopolysiloxane resins be different from component of the present invention (B), can not provide to prevent that fully silicone components from transferring on the adherend surface.In addition, compare with composition of the present invention, the composition of Comparative Examples 3 (it is the silicone-based pressure-sensitive adhesive composition that solidifies by known addition reaction) does not provide the transfer that prevents fully silicone components yet.
[table 1]
Claims (5)
1. the silicone-based pressure-sensitive adhesive composition of a peroxide-curable, it comprises component (A)-(C), wherein:
(A) consumption be 100 weight parts on two molecular end, all have a diorganopolysiloxaneand with the alkenyl of silicon bonding with general formula (1) expression:
R wherein
1The monovalent saturated hydrocarbon group that expression does not replace or replaces, R
2Expression has the alkenyl of 2-10 carbon atom, and k is the integer greater than 2000 to 100,000, and s is positive integer, and they satisfy following condition: 0.0＜s/ (k+s)≤0.02;
(B) consumption be the 25-100 weight part in a molecule, have one or more silanol groups (OH) and by R
3 2(OH) SiO
1/2Unit, R
3 3SiO
1/2Unit and SiO
4/2The organopolysiloxane resins that the unit forms, wherein R
3Expression has the univalence hydrocarbyl that does not replace or replace of 1-10 carbon atom independently; With
(C) one or more organic peroxide compounds of catalytic amount;
R in the aforementioned component (B) wherein
3 2(OH) SiO
1/2Unit and R
3 3SiO
1/2Unit sum and SiO
4/2The ratio of unit is in the 0.6-0.9 scope; With
90-99mol% is that methyl and 1-5mol% are silanol groups in the middle of all functional groups that wherein comprise in the aforementioned component (B).
2. the silicone-based pressure-sensitive adhesive composition of the peroxide-curable of claim 1 further comprises organic solvent (D).
3. self adhesive tape, it comprises carrier film and the pressure sensitive adhesive layer that obtains by solidifying any one the silicone-based pressure-sensitive adhesive composition of peroxide-curable of claim 1-2.
4. the self adhesive tape of claim 3, it is the masking belt that uses in thermal treatment.
5. the self adhesive tape of claim 3, it is the masking belt that uses in scope is thermal treatment under 200-300 ℃ the temperature.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP347679/2006 | 2006-12-25 | ||
| JP2006347679A JP5049584B2 (en) | 2006-12-25 | 2006-12-25 | Peroxide-curing silicone pressure-sensitive adhesive composition and pressure-sensitive adhesive tape |
| PCT/JP2007/075334 WO2008081951A1 (en) | 2006-12-25 | 2007-12-20 | Peroxide-curable silicone-based pressure-sensitive adhesive composition and adhesive tape |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101558128A CN101558128A (en) | 2009-10-14 |
| CN101558128B true CN101558128B (en) | 2013-01-02 |
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ID=39190514
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2007800457284A Active CN101558128B (en) | 2006-12-25 | 2007-12-20 | Peroxide-curable silicone-based pressure-sensitive adhesive composition and adhesive tape |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20100104865A1 (en) |
| EP (1) | EP2121867B1 (en) |
| JP (1) | JP5049584B2 (en) |
| KR (1) | KR101460548B1 (en) |
| CN (1) | CN101558128B (en) |
| TW (1) | TWI447197B (en) |
| WO (1) | WO2008081951A1 (en) |
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| JP5842433B2 (en) * | 2011-07-25 | 2016-01-13 | デクセリアルズ株式会社 | Method for measuring dynamic viscoelasticity of particulate materials |
| CN103087642A (en) * | 2011-11-03 | 2013-05-08 | 阿特斯(中国)投资有限公司 | Solar cell packaging adhesive film and preparation method thereof |
| CN103450840A (en) * | 2013-01-24 | 2013-12-18 | 际华三五零二职业装有限公司 | Preparation method of silica gel for glove plant gum |
| BR102014017354B1 (en) | 2013-07-30 | 2021-06-29 | Rohm And Haas Company | COMPOSITION, AND, METHOD FOR PREPARING A COMPOSITION |
| JP6265772B2 (en) | 2014-02-13 | 2018-01-24 | 日東電工株式会社 | Silicone pressure-sensitive adhesive composition, pressure-sensitive adhesive tape, and method for producing pressure-sensitive adhesive tape |
| JP6348434B2 (en) * | 2014-03-28 | 2018-06-27 | 信越化学工業株式会社 | Silicone pressure-sensitive adhesive composition, production method thereof, and pressure-sensitive adhesive film |
| WO2016061121A1 (en) * | 2014-10-13 | 2016-04-21 | Avery Dennison Corporation | Weldable and vibration damping silicone adhesives |
| KR20180085009A (en) * | 2015-12-15 | 2018-07-25 | 다우 실리콘즈 코포레이션 | Silicone pressure sensitive adhesive composition |
| WO2018132941A1 (en) * | 2017-01-17 | 2018-07-26 | Dow (Shanghai) Holding Co., Ltd. | Method for making silicone pressure sensitive adhesive |
| DE102017202623A1 (en) * | 2017-02-17 | 2018-08-23 | Tesa Se | Vibration-damping silicone pressure-sensitive adhesive |
| DE102017202624A1 (en) * | 2017-02-17 | 2018-08-23 | Tesa Se | Vibration-damping silicone pressure-sensitive adhesive |
| TWI767036B (en) * | 2017-08-25 | 2022-06-11 | 美商陶氏有機矽公司 | Silicone pressure-sensitive adhesive composition |
| KR102422196B1 (en) * | 2017-09-05 | 2022-07-20 | 가부시키가이샤 데라오카 세이사쿠쇼 | Silicone-based pressure-sensitive adhesive composition and adhesive tape |
| JP7050704B2 (en) * | 2019-02-07 | 2022-04-08 | 信越化学工業株式会社 | Thermally conductive silicone rubber sheet with thermally conductive adhesive layer |
| JP7270792B2 (en) * | 2019-02-07 | 2023-05-10 | 信越化学工業株式会社 | Thermally conductive silicone rubber sheet with thermally conductive adhesive layer |
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| JP2734809B2 (en) * | 1991-05-09 | 1998-04-02 | 信越化学工業株式会社 | Silicone adhesive composition |
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| JP2006213810A (en) * | 2005-02-03 | 2006-08-17 | Shin Etsu Chem Co Ltd | Silicone composition for pressure-sensitive adhesive and pressure-sensitive adhesive tape obtained from the same |
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2006
- 2006-12-25 JP JP2006347679A patent/JP5049584B2/en active Active
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- 2007-12-20 EP EP07851128.4A patent/EP2121867B1/en active Active
- 2007-12-20 US US12/520,611 patent/US20100104865A1/en not_active Abandoned
- 2007-12-20 WO PCT/JP2007/075334 patent/WO2008081951A1/en active Application Filing
- 2007-12-20 KR KR1020097015706A patent/KR101460548B1/en active IP Right Grant
- 2007-12-25 TW TW096149973A patent/TWI447197B/en not_active IP Right Cessation
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2121867A1 (en) | 2009-11-25 |
| US20100104865A1 (en) | 2010-04-29 |
| TW200900479A (en) | 2009-01-01 |
| EP2121867B1 (en) | 2013-08-28 |
| JP5049584B2 (en) | 2012-10-17 |
| WO2008081951A1 (en) | 2008-07-10 |
| TWI447197B (en) | 2014-08-01 |
| KR101460548B1 (en) | 2014-11-12 |
| JP2008156496A (en) | 2008-07-10 |
| CN101558128A (en) | 2009-10-14 |
| KR20090101364A (en) | 2009-09-25 |
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